Titanium-mediated cyclopropanation of N,N-dibenzylcarboxamides towards functionally substituted 2-(1′-aminocyclopropyl)acetic acids

Synthesis

Volumn , Issue 12, 2005, Pages 2008-2014

  Brackmann, Farina ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Amino acids; Cyclopropanes; Low valent titanium; Medicinal chemistry; Structure elucidation

Indexed keywords

ACETIC ACID; AMINO ACIDS; CRYSTALLINE MATERIALS; ISOMERS; MIXTURES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TITANIUM COMPOUNDS;

CYCLOPROPANES; LOW VALENT TITANIUM; MEDICINAL CHEMISTRY; STRUCTURE ELUCIDATION;

AMINES;

3,6 BIS(N TERT BUTOXYCARBONYLAMINO) 3,4 METHANOHEXANOIC ACID; CARBAMIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; HEXANOIC ACID; N,N DIBENZYL N [1 (2 BENZYLOXYETHYL) 2 (2 HYDROXYETHYL)CYCLOPROPYL]AMINE; TERT BUTYL N [1 (2 BENZYLOXYETHYL) 2 (2 HYDROXYETHYL)CYCLOPROPYL]CARBAMATE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTALLIZATION; CYCLOPROPANATION; DEBENZYLATION; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 23744451247     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869904     Document Type: Article

References (34)

1. (a) Part 112 in the series: Cyclopropyl Building Blocks for Organic Synthesis, (a) For Part 111 see: Brackmann, F.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem. 2005, in press.
2. (b) Part 110: Knoke, M.; de Meijere, A. Eur. J. Org. Chem. 2005, in press.
3. (a) Salaün, J. Top. Curr. Chem. 2000, 207, 1.
4. (b) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645.
5. (c) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
6. (d) Burgess, K.; Ho, K. K.; Moyesherman, D. Synlett 1994, 575.
7. Review: Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
8. (a) Funabashi, Y.; Tsubotani, S.; Koyama, K.; Katayama, N.; Harada, S. Tetrahedron 1993, 49, 13.
9. Total syntheses see: (b) Yuan, C.; Williams, R. M. J. Am. Chem. Soc. 1997, 119, 11777.
10. (c) Sokolov, V. V.; Kozhushkov, S. I.; Nikolskaya, S.; Belov, V. N.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem. 1998, 777.
11. (d) Belov, V. N.; Brands, M.; Raddatz, S.; Krüger, J.; Nikolskaya, S.; Sokolov, V. V.; de Meijere, A. Tetrahedron 2004, 60, 7579.
12. (a) German Offen., No. DE 19838998A1, 1998; Chem. Abstr. 2000, 132, 180819z.
13. (b) German Offen., No. DE 10141271A1, 2003; Chem. Abstr. 2003, 138, 205087.
14. (c) Kordes, M.; Brands, M.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem. 2005, in press.
15. Kordes, M. Dissertation; Universität Göttingen: Germany, 1999.
16. Kordes, M.; Winsel, H.; de Meijere, A. Eur. J. Org. Chem. 2000, 3235.
17. (a) Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413;
18. Angew. Chem. 1996, 108, 491.
19. Reviews: (b) Kulinkovich, O. G.; de Meijere, A. Chem. Rev. 2000, 100, 2789.
20. (c) Breit, B. J. Prakt. Chem. 2000, 342, 211.
21. (d) Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835.
22. (e) Sato, F.; Urabe, H.; Okamoto, S. Synlett 2000, 753.
23. (f) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. In Titanium and Zirconium in Organic Synthesis; Marek, L, Ed.; Wiley-VCH: Weinheim, 2002, 390.
24. (g) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. J. Organomet. Chem. 2004, 689, 2033.
25. Reviews: (a) Mitsunobu, O. Synthesis 1981, 1.
26. (b) Hughes, D. L. Org. React. (N.Y.) 1992, 42, 335.
27. (c) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127.
28. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
29. (b) Review: Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
30. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited as supplementary publication no. CCDC-260818 with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK Fax: (+44)1223-336-033; E-mail: deposit@ccdc.cam.ac. uk.
31. (a) Rail, M.; Harmony, M. D.; Cassada, D. A.; Staley, S. W. J. Am. Chem. Soc. 1986, 108, 6184.
32. (b) de Meijere, A.; Chaplinski, V.; Winsel, H.; Kusnetsov, M. A.; Rademacher, P.; Boese, R.; Haumann, T.; Traetteberg, M.; von R. Schleyer, P.; Zywietz, T.; Jiao, H.; Merstetter, P.; Gerson, F. Angew. Chem. Int. Ed. 1999, 38, 2430;
33. Angew. Chem. 1999, 111, 2582.
34. Wolff, H. Org. React. (N.Y.) 1947, 3, 307.